Реакция #8644

Уравнение реакции

hexabromospirobifluorene

biphenylboronic acid

→

2,2′,4,4′,7,7′-hexabiphenylyl-9,9′-spirobifluorene

Растворители

toluene

toluene

potassium carbonate

Условия реакции

Обработка

1. 1
   ДругоеIn a 250 ml two-necked flask fitted
2. 2
   Температураwith reflux condenser and precision glass stirrer
3. 3
   ТемператураThe mixture is refluxed under nitrogen
4. 4
   Температураunder reflux for 7 hours
5. 5
   Фильтрацияthe cooled solution is filtered
6. 6
   Экстракцияthe filtrate is extracted twice
7. 7
   workup.STIRRINGby shaking with water (
8. 8
   Другоеthe phase separation, chloroform
9. 9
   workup.ADDITIONis added)
10. 10
    СушкаThe organic phase is dried over sodium sulfate
11. 11
    Фильтрацияfiltered through a short column of silica gel
12. 12
    Другоеsubsequently evaporated on a rotary evaporator
13. 13
    ДругоеThe product is further purified by recrystallization from dichloromethane/pentane

Методика

In a 250 ml two-necked flask fitted with reflux condenser and precision glass stirrer, 1.6 g of hexabromospirobifluorene and 3 g of biphenylboronic acid are slurried in a mixture of 50 ml of toluene and 50 ml of 1 M potassium carbonate solution. The mixture is refluxed under nitrogen and 115 mg of tetrakis(triphenylphosphine)palladium in 5 ml of toluene are added. The mixture is boiled under reflux for 7 hours while stirring. After the reaction is complete, the cooled solution is filtered and the filtrate is extracted twice by shaking with water (to improve the phase separation, chloroform is added). The organic phase is dried over sodium sulfate, filtered through a short column of silica gel and subsequently evaporated on a rotary evaporator. The product is further purified by recrystallization from dichloromethane/pentane. This gives 2 g (80%) of colorless crystals which fluoresce blue under UV illumination.

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